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Stolle is notable for being the only male player in history to have lost his first five Grand Slam singles finals, the fifth of which he led by two sets to love. However, Stolle went on to win two Grand Slam tournament singles titles, the 1965 French Championships and the 1966 US Championships, but failed to win Wimbledon and the Australian Championships, finishing as runner-up in these tournaments and losing to compatriot Roy Emerson on no fewer than five occasions. Lance Tingay of The Daily Telegraph ranked Stolle as World No. 2 in 1966.[2]

As a member of the Australian Davis Cup team Stolle won the Davis Cup title in 1964,[4] 1965 and 1966.[5] In 1964 Stolle and Emerson were briefly suspended from the Australian Davis Cup team for going on an overseas tour in defiance of a Lawn Tennis Association of Australia order to remain in Australia until April.[6]

Stolle turned professional in 1966,[1] and as a pro won two singles and 13 doubles titles. He earned about US$500,000 in career prize money.[7]

For many years, Stolle did TV commentary for CBS and other tennis broadcasts. He currently provides commentary on Grand Slam tennis tournaments for Australia's Fox Sports and the Nine Network. He is also part of the commentary team for the Hopman Cup on One HD.